


Sick Day

by Disneyfan1234



Category: Jessie (TV)
Genre: Dildos, Dream Sex, F/F, Fingering, Lesbian Sex, Masturbation, Mutual Masturbation, Seduction, Shower Sex, sick day
Language: English
Status: Completed
Published: 2016-01-01
Updated: 2016-09-05
Packaged: 2018-05-10 21:13:03
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 2,810
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5601187
Author URL: https://archiveofourown.org/users/Disneyfan1234/pseuds/Disneyfan1234
Summary: <blockquote class="userstuff">
              <p>Emma doesn't want to go to school. What she really wants is her nanny, Jessie.</p>
            </blockquote>





	1. Sick Day

"Emma, hurry up! Your going to be late for school!" Jessie calls up the staircase of the Ross's apartment.  
"I'm not going, I'm sick." Emma yells down to her nanny.  
"Fine, I'm going to take your siblings to school, then I'll be up there to check on you. You better be sick." Jessie says as she steps into the elevator with the other three Ross's. 

Emma is relieved when she hears the elevator doors close. She's skipping school! She feels rebellious, but she doesn't want to disappoint Jessie. She tries to think of a way to trick Jessie into thinking she is really sick. She could eat crickets with Mrs. Kipling, eat some of Bertram's leftover goulash, or walk into Luke's room. She considers her options until she remembers what she learned about in Health class. Masturbation causes an increase in body temperature, speeds up heart rate and will make it harder for Emma to speak clearly. It was perfect, and more fun than her other options. She made her decision. Emma snakes her hand down her body, pausing only slightly near her breasts. She slides her hand into her favorite panties and rubs herself. Her touch heats her insides and she is confident her plan will work. She slides one of her fingers in and instantly feels her heart speed up.  
"Mmmmm." Emma can't help but moan. Emma loves masturbating, but she usually can't verbally express it due to her full house. Emma slides another finger in herself. Sometimes Emma wonders what it's like to actually do it with a guy, or better yet, a girl. Sometimes when Emma fingers herself, she can't help but think of Jessie. Jessie and her red hair, and her tits, and her face that makes Emma wetter just thinking about it. As her nipples harden at the thought of her beautiful nanny, the elevator doors open.

Jessie was worried about Emma. Her heartbeat was faster than it should have been and her forehead was hot.  
"Is there anything I can get you?" Jessie asks.  
"Jessie." Emma says weakly.  
"Yes dear?" Jessie replies, leaning towards the blonde teen.  
"Take me. Right here. Right now." Emma says as she locks lips with Jessie in a passionate kiss.  
"I thought you were sick." Jessie asked, breaking away from the kiss.  
"I was faking. I was masturbating to make it seem like I was sick."  
"Clever girl." Jessie says, reinitiating the kiss. Emma couldn't believe what she was doing. She was kissing her sexy redhead nanny and she was loving it. Emma feels a hand brush against her sex, sending pleasure through her body. "Jessie, I'm ready." Emma says. Jessie nods.  
"Let's get this shirt off first." Jessie says as she pulls Emma's shirt up over her head. Jessie then takes off her own top, showing her large boobs in their red bra to the staring blonde.  
"Jessie, I've waited for this day since I met you." Emma says, feeling her core heat.  
"Stop talking." Jessie says as she places a singular finger on Emma's lips and slinks down towards Emma's womanhood. Jessie peels of the soaked panties and licks the blondes treasure. Jessie then takes two of her fingers and, after sexily sucking them, shoves them both into Emma.  
"Ooohh...shit." Emma moans at the sudden intrusion. Jessie has begun pumping in and out of Emma, causing Emma to moan louder. Jessie takes her other hand and begins to play with her own clitoris.  
"Jessie...yes!" Emma moans, feeling herself close to orgasm. Jessie knows Emma is close, so to finish the blonde teen, Jessie whispers into Emma's ear.  
"I want you to come all over my fingers you filthy slut. Skipping school so you could be pleasured by your smoking hot nanny. Filthy. I'm then going to shove my fingers so far down your throat, you are going to choke on your own juices and it will be so hot I'll come on my fingers and shove them down your throat as well." This dirty talk pushed Emma over the edge. Jessie felt her cave tighten around her fingers as they were coated by Emma's secret sauce.  
"Open wide." Jessie says as she shoves her fingers down the teenager's throat.  
"Ack." Emma chokes as the liquids are pooled into her throat. She loves how she tastes, but she can't wait to taste her nanny's cum.  
"Emma!" Jessie yells as she comes on her own fingers. She pulls them out of her dripping kitty and has Emma suck off the juices.  
"Emma." Jessie says.  
"Jessie." Emma says.  
"You need to be sick more often." Jessie says with a kiss on Emma's forehead.  
"Days not over yet, babe." Emma says back with a giggle. Best sick day ever.


	2. Shower Time

"Jessie!" Emma yells.  
"What?" Jessie's head peeks into the doorway of the Ross's bathroom.  
"I'm going to take a shower. Would you like to join?"  
"Of course!" Jessie says. They both enter the shower immediately since they hadn't bothered to put on clothes. Emma bends down to turn on the shower. Seeing the opportunity, Jessie grabs the blonde's ass and gives it a smack.  
"Woah there cowgirl! Is someone excited?" As the water starts to pour on the girls, Emma turns and locks lips with her nanny. Jessie moves her hand down Emma's back to her bubbly butt. As she grabs it, she can feel the gasp from the blonde. Jessie next moves to Emma's girlhood. She can't tell if it's wet due to the shower or her excitement. She assumes both and puts two fingers in. Emma breaks away from the kiss to breathe.  
"Oh yes Jess! Don't stop!"  
"I may if I remain untouched." Jessie teases.  
"Of course." The blonde grabs the shower head and lowers it to Jessie's taint. The water sprays all over Jessie's folds, making them wetter then it had already been.  
"Oh yeah! I'm so wet! Ahh!"  
"Jessie, I want you to make me come!" Emma begs, but Jessie is too distracted by the blonde's perky A cup tits. Normally, Jessie loves trying to get a peek at Emma's bust, but seeing them glisten with the water is so hot.  
"Jessie! I'm almost...!" Emma yells, breaking Jessie from her trance, resulting in another finger entering Emma.  
"Jessie!" The build up of pleasure from the water and the look of pure ecstasy on Emma's face pushes Jessie over at the same time as Emma.  
"Emma!"  
"Jessie!" Both girls yell as their juices squirt all over the place.  
"Oh shit Jessie, that was good."  
"It's a good thing you're taking a shower, Emma, because you're a very filthy girl." Jessie said, kissing Emma once again.


	3. Dreams

**Summary for the Chapter:**

> Turns out it was all a dream, but reality may not stray that far from fantasy.

Jessie sits up in her bed. Her clock reads 12:34, the middle of the night. She looks around her darkened room. She was all alone.   
'Was that a dream?' Jessie wondered. Then she acknowledged the stain on her bedsheets.   
"Shit, I'll have to clean those." Jessie curses. Laying back down, Jessie recounts the events of her dream. Jessie remembers how Emma looked, sounded and tasted. As she thinks, she feels herself get wet again.   
'Well, my sheets are already wet. Guess there's nothing holding me back.' Jessie tells herself as she moves her hand along her womanhood. One of Jessie's favorite part of sleeping naked was that if she ever felt the need, there was nothing in her way. Jessie remembers how Emma had been so desperate for her, skipping school to spend a day alone with her sexy nanny. Thinking of Emma's moans, Jessie inserts her first fingers inside herself. 

Little did Jessie know, she wasn't the only girl pleasuring herself in the suite. Down the hall, Emma had one hand in her thin pink panties, the other was holding her phone. Emma was sliding through Google images looking at nudes of this celebrity named Debby Ryan, who coincidentally looked exactly like her nanny Jessie. Emma may have even contributed a couple of the pictures. Just the way Debby smiled as she had multiple dicks shoved inside her, or the way her tits were so round. Emma imagined them being Jessie's, bouncing up and down as she rubbed herself against Emma. Emma had considered skipping school just to spend the day with her nanny. As Emma imagined having sex with Jessie, she felt herself tighten. This was going to be a good one.

Jessie imagined the Emma's head between her legs, eating her out. She imagined pulling the blonde's hair as her tongue navigated her folds. She put her entire hand inside her, feeling herself near release, when she hears Emma finish down the hall.  
"Mm yes Jessie, I love you! Hell yeah."   
Emma yells as she cums to a picture of Debby's face covered in cum, unknowingly setting off Jessie.   
"Emmmmmaaaa... I love you. Too." Jessie squirts onto her already wet bedsheets. As the redhead drifts off to sleep, she comes up with a plan to make her dreams a reality.


	4. Checkup

The next morning, Jessie serves the Ross children their breakfast before they go to school. As they are eating, Jessie can't keep herself from looking at Emma. She she was wearing a pink plaid shirt and white shorts that totally showed off her assets. Jessie hid behind the counter so that she could lightly touch herself. She couldn't wait to start her plan to seduce Emma Ross.   
"Hey Emma, do you feel alright? You look kind of sick. Come to the bathroom, I'll check to see if you can go to school today." Jessie says, lightly rubbing herself from behind the counter. Jessie follows the blonde to the bathroom, watching her ass the entire way.   
Once the two girls were in the bathroom Emma turns around and asks the question.   
"What's this about. I know I don't feel sick, so why did you want me in here?"   
In response, Jessie forcefully pushes the younger woman against the wall, getting really close.   
"I heard you last night. What were you doing last night?" Jessie questions, her face mere inches from the blonde. Regardless, Emma couldn't hide her arousal. Her sexy nanny had her pressed against a wall with her beautiful face so close to her own.   
"I was fingering myself to you. What are you going to do about it, punish me?"  
"You wish." Jessie whispers in Emma's ear before lightly biting it. Jessie moves one hand down to the blondes tight little snatch while keeping the other hand pressed against the blonde, holding her against the wall.   
"Oh Jessie. I know you've been wanting this for as long as I have. Wanting my tight body shaking in your arms. I heard you last night too." Emma whispers.  
"Good." Jessie says in a whisper as she pulls down Emma's white shorts.   
"Are you wet already? I've hardly even started." Jessie teases, noticing the growing wet patch on Emma's panties. Once Jessie pulls down Emma's moist panties, the nanny gets to work. She goes straight into Emma's cunt, licking and biting whatever she could. Jessie also decides she can't go untouched, so she goes to touch herself, but before she gets to her desperate kitty, Emma grabs her hand.   
"Why would you touch yourself when you can use my little gift to you. Look under the sink." Emma says, pointing to the cabinet under the sink. Jessie crawls over to the cabinet, purposefully swaying her ass in a way that drove Emma crazy. She opens the cabinet and looks around, only to be stunned by what she finds.  
"Holy shit." Jessie gasps, pulling an 8 inch dildo out of the cabinet. "Why is this in here?"   
"I'm a teenager, I've got one hidden in every room."   
"You naughty slut." Jessie says examining the member. It was pink and had a suction cup on the bottom.   
"Now, where were we?" Emma asks, desperate for Jessie to continue her work.   
"I was checking to see if you were sick, and you currently appear very flustered." Jessie says, slowly crawling back to the blonde.  
"Jessie, I'm sick of this teasing shit. Make me cum or I'll do it myself."   
"Impatient much?" Jessie says, sticking the dildo to the floor. As Jessie slowly eases herself onto the dildo, she brushes a hand against Emma's clit, sending a jolt through the blonde. Once Jessie has eased the entire length inside her, she continues her exploration of Emma's cunt.   
"Mmm... Jessie. That's good..." Emma moans, groping herself through her pink flannel. Jessie begins bouncing on the dildo, causing Emma's arousal to increase.   
"Oh Emma, do you like this? Am I better than your fingers?"   
"Yes, Jessie. YES!!" Emma yells as she experiences one of the best orgasms she's ever had.   
"Keep bouncing on that cock." Emma commands after she settles down. She goes and kisses the flustered nanny, only to surprise her when Emma grabs her throat and squeezes.  
"Emma..." Jessie moans, trying to breathe as normally as she can.  
"You like this, don't you. You like that cock in you. You like my hand around your throat. You filthy slut."   
"Emma...Emma!!" Jessie moans the blondes name as she releases all the pressure that has built up inside her.   
"Jessie," Emma says, kneeling down so she's eye level with the redhead. "I think I love you."  
"I love you too."


	5. The End

"Mom, can I ride with Jessie on her way to the airport? Please." Emma asks Christina Ross in the lobby after they have all gotten off the elevator.  
"Why?" Christina asks, oblivious of the affair between her daughter and nanny.  
"I just want to have a more personal goodbye. Please." Emma begs, praying that she didn't wear Jessie's favorite lingerie for nothing.  
"I guess that's fine."  
"Thanks mom! I love you!"

Jessie waves to the Ross family one last time before she gets into the limo with Emma. As soon as they are out of sight of the family, they looked at each other.  
"I guess this is it." Jessie says, scanning the blonde girl that had grown up so much in the past four years.  
"I guess so." Emma says, looking at the nanny who has acted as both a mother and a lover. She can't believe that Jessie is actually leaving them, leaving her, to go start her career as an actor in Hollywood. They share a moment of silence to study each other so that they miss no detail of the other when they reflect on their time together.  
"What are we waiting for." Emma says, wanting to make love to her nanny and best friend one last time.  
"I guess this." Jessie says, leaning over and gently initiates a kiss. Emma gently kisses back, savoring these last moments together. Jessie picks up the younger girl out of her seat and, without breaking the kiss, sets her on her lap.  
"Jessie I..."  
"No talking, just...enjoy this." Jessie says, silencing the blonde with another kiss, but this time, slightly more forceful, but no less passionate. Emma was getting tired of this build up. As she took of her top, showing off her tits, Jessie truly realized how much Emma has grown and developed, both physically and emotionally. She was wearing Jessie's favorite lingerie, and Jessie appreciated it.  
"You remembered." Jessie says.  
"I remembered that you loved this underwear nearly as much as you love what's underneath." Emma says, unclipping her bra and letting it fall from her A cup size boobs. Jessie is going to miss this girl. Jessie grabs the blondes ass and begins to slide her across her lap, causing Emma's taint to rub against the nanny's leg.  
"Oh Jessie." Emma moans, wishing that this didn't have to be the last time. She brushes a hand against Jessie's kitty, all while continuing to grind on Jessie's leg.  
"Come on Emma, make me miss you." Jessie says, encouraging Emma as she reaches her hand into her nanny's pants and begins to probe around with her fingers. While Emma grinds in Jessie's lap, she slides two of her fingers inside her nanny. Noticing that Jessie is barely affected by the two fingers, she puts in two more while she rubes Jessie's clit with her thumb. This gets a reaction out of the nanny.  
"Ohh..." Jessie pouts, becoming more forceful on Emma's hips, causing the blonde to increase the speed of her grind.  
"Jessie..." Emma moans as her pressure builds inside her. The blonde goes to suck on the redheads tits as she maxes out. Her orgasm is strong, causing her to bite down on Jessie's tit and curl her fingers inside her.  
"Emma!" Jessie screams as she finally gets her release. After they both come down and Emma is cleaning her fingers, Jessie looks into her eyes, tears beginning to form.  
"Emma, I love you."  
Emma looks back at her lover, so close to tears.  
"Jessie, I love you too."

**Notes for the Chapter:**

> This story is done, but I really enjoyed writing about this show. Should I write about Jessie some more, or should I change to a different Disney Channel show?


End file.
